This invention relates in general to the process for copolymerizing allyl halides (mono-olefinic allyl type mono-halide) with polymerizable unsaturated organic compounds such as vinyl monomers and diene monomers by utilizing an oxidized silicon catalyst.
The process to polymerize allyl halides in the presence of an oxidized silicon catalyst may be found in U.S. Pat. No. 4,020,259.
Various oxidated silicon compounds such as silicon acids, silica, silicates containing silicon acid radicals and silicates that will react with the halides in the allyl type halides to produce silicon acid radicals of mixtures thereof may be used as the catalyst, and in some cases, react with allyl halides to form allyl type halide silicate polymers.
Various silicon acids such as silicoformic acid, polysilicoformic acid, hydrated silica and natural occuring silicates containing free silicic acid radicals may be used as the catalyst in this invention.
Various alkali metal silicates and alkaline earth metal silicates such as sodium silicate, potassium silicate, lithium silicate, calcium silicate cadmium silicate, barium silicate, zinc silicate, barium silicate, magnesium silicate, aluminum silicate, etc. maybe used as the catalyst in this process.
Some of the natural occuring silicates that maybe used in this invention are clay, kaolin, silica, talc, asbestos, natrolite, garnet, mica, feldspar, beryl, diatomaceous earth, etc., and mixtures thereof. The natural occuring silicates may be treated with a dilute mineral acid to produce more active silicic acid radicals present in the silicates.
Allyl halides may be produced by the addition of a halide to propylene. Methylallyl halides may be produced by the addition of a halide to isobutylene. Other compounds with the combination of --C.dbd.C--, which is known as the allylic system, may be used in this invention. Allyl chloride is the preferred allyl halide.
Various mono-olefinic allyl mono-halide with the essential grouping of atoms which may be represented as ##STR1## wherein R is a hydrogen or a C.sub.1 to C.sub.4 allkyl group and wherein X represents a halogen atom. Furthermore, these compounds contain only one olefinic group of which one of the unsaturated carbon atoms contains at least one hydrogen atom per molecule.
Representive examples of mono-olefinic allyl mono-halides are such compounds as allyl chloride, allyl bromide, crotyl chloride, crotyl iodide, beta-methylallyl chloride, beta-methylallyl bromide, methyl vinyl carbinyl chloride, methyl vinyl carbinyl fluoride, alpha-dimethyl-allyl chloride, beta-cyclohexylallyl chloride, cinnamyl chloride, beta-ethylcrotyl chloride, beta-phenyl allyl bromide, alpha-dicyclohexylallyl chloride, beta-propylallyl iodide, beta-phenyl-allyl chloride, beta-cyclohexylallyl fluoride, 2-chloromethyl butene-1, 2-chloromethyl pentene-1, 2-chloromethyl hexene-1 and mixtures thereof.